picrotoxinin   

GtoPdb Ligand ID: 2291

2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 85.36
Molecular weight 292.09
XLogP -0.47
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(=C)C1C2OC(=O)C1C1(C3(C2OC(=O)C23C(C1)O2)C)O
Isomeric SMILES CC(=C)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1([C@]3([C@@H]2OC(=O)[C@]23[C@@H](C1)O2)C)O
InChI InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1
InChI Key PIMZUZSSNYHVCU-YKWPQBAZSA-N
References
1. Lynch JW, Rajendra S, Barry PH, Schofield PR. (1995)
Mutations affecting the glycine receptor agonist transduction mechanism convert the competitive antagonist, picrotoxin, into an allosteric potentiator.
J. Biol. Chem., 270 (23): 13799-806. [PMID:7775436]
2. Pribilla I, Takagi T, Langosch D, Bormann J, Betz H. (1992)
The atypical M2 segment of the beta subunit confers picrotoxinin resistance to inhibitory glycine receptor channels.
EMBO J., 11 (12): 4305-11. [PMID:1385113]
3. Thompson AJ, Duke RK, Lummis SC. (2011)
Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor.
Mol. Pharmacol., 80 (1): 183-90. [PMID:21505038]
4. Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC. (2011)
Ginkgolide B and bilobalide block the pore of the 5-HT(3) receptor at a location that overlaps the picrotoxin binding site.
Neuropharmacology, 60 (2-3): 488-95. [PMID:21059362]
5. Yang Z, Cromer BA, Harvey RJ, Parker MW, Lynch JW. (2007)
A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore.
J. Neurochem., 103 (2): 580-9. [PMID:17714449]